Boron compounds as inhibitors of lipoxygenase and the lipoxygenase pathway, and preparation and use thereof
AssigneeUniversitäT Leipzig
InventorsEvamarie HEY-HAWKINS, Robert KUHNERT
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Abstract
The invention relates to chemical compound of the general structure [A-R3—X—R4] where A=[R1-R2] or [R1] R1=aryl, heteroaryl R2=alkyl, aryl, heteroaryl, carbonyl, thiocarbonyl, alkyl ester, alkyl thioester R3=O, S, NH X=closo- or nido-boron cluster R4= where Z=OH, SH, NH2 where R5 is selected from H, alkyl, aryl, heteroaryl, alkyl ether, alkyl thioether, alkylamine and R6 is selected from alkyl, aryl, heteroaryl, alkyl ether, alkyl thioether, alkylamine and where R3 and R4 are in meta or para positions to one another, to a process for preparation thereof and to the use thereof, especially in medicine, for example in the inhibition of lipoxygenase.
Claims14
Chemical compound of general structure
- [A-R3—X—R4]
- where
- A=[R1-R2] or [R1]
- R1=aryl, heteroaryl
- R2=alkyl, aryl, heteroaryl, carbonyl, thiocarbonyl, alkyl ester, alkyl thioester
- R3=O, S, NH
- X=closo- or nido-boron cluster
- R4=
- where Z=OH, SH, NH2
- where R5 is selected from H, alkyl, aryl, heteroaryl, alkyl ether, alkyl thioether, alkylamine
- and R6 is selected from alkyl, aryl, heteroaryl, alkyl ether, alkyl thioether, alkylamine
- and where R3 and R4 are in meta or para positions in relation to one another.
Method for preparing a chemical compound of general formula
- [A-R3—X—R4]
- where
- A=[R1-R2] or [R1]
- R1=aryl, heteroaryl
- R2=alkyl, aryl, heteroaryl, carbonyl, thiocarbonyl, alkyl ester, alkyl thioester
- R3=O, S, NH
- X=closo- or nido-boron cluster
- R4=
- where Z=OH, SH, NH2
- where R5 is selected from H, alkyl, aryl, heteroaryl, alkyl ether, alkyl thioether, alkylamine
- and R6 is selected from alkyl, aryl, heteroaryl, alkyl ether, alkyl thioether, alkylamine
- and where R3 and R4 are in meta or para positions in relation to one another,
- comprising the steps of:
- a) hydroxyalkylating or thioalkylating or aminoalkylating the cluster X,
- b) hydroxylating or thiolating or aminating the boron-containing cluster X,
- so as to form an intermediate compound of general formula [H—R3—X—R4]
- where
- R3=O, S, NH
- X=closo- or nido-boron cluster
- R4=
- where Z=OH, SH, NH2
- where R5 is selected from H, alkyl, aryl, heteroaryl, alkyl ether, alkyl thioether, alkylamine
- and R6 is selected from alkyl, aryl, heteroaryl, alkyl ether, alkyl thioether, alkylamine
- and where R3 and R4 are in meta or para positions in relation to one another
- c) selectively etherifying or esterifying H—R3 in order to introduce A,
- wherein steps a) and b) can be interchanged as desired.
Dependencies are inferred from the claim text.